Water → HCID 69436265, compound

HRID 404927Notes

Reaction equation

HRID 404927 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]#[N:8])=[CH:5][N:6]=1.[NH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[NH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][C:2]1[S:3][C:4]([C:7]#[N:8])=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 14852222-Chlorothiazole-5-carbonitrile

Product 1

HCID 69436265HCID 69436265, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-chloro-thiazole-5-carbonitrile (1.09 g, 7.5 mmol; prepared as described in WO 01/17995, p. 103) and 3-amino phenol (820 mg, 7.5 mmol) were combined in N,N-dimethyl formamide (5 mL). To this solution, K2CO3 (3.1 g, 22.5 mmol) was added and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with ethyl acetate (2×). The combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by flash column chromatography (ethyl acetate:hexanes; 5%-75% ethyl acetate gradient) to give the title compound (1.63 g, 7.5 mmol, 100%) as a white solid. MS (ESI APCI) m/z 217.9 (M+H+), 1H NMR (300 MHz, DMSO-d6) δ 8.24 (s, 1H) 7.14 (t, J=7.91 Hz, 2H) 6.40-6.64 (m, 2H) 5.54 (s, 2H).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified by flash column chromatography (ethyl acetate:hexanes; 5%-75% ethyl acetate gradient)

Sources & evidence

ORD record
ord-865183b9f4c849f4b4b0c75e889ea277
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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